14368-55-9Relevant academic research and scientific papers
Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3
Fukumoto, Yoshiya,Tamura, Yuto,Iyori, Yasuaki,Chatani, Naoto
, p. 3161 - 3167 (2016/05/19)
The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction system is applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively. The catalytic cycle involves the formation of a vinylidenerhodium complex as a key intermediate.
Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones
Jinzaki, Takaaki,Arakawa, Mitsuru,Kinoshita, Hidenori,Ichikawa, Junji,Miura, Katsukiyo
supporting information, p. 3750 - 3753 (2013/08/23)
α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su
Reaction of the electrogenerated cyanomethyl anion with carbonyl compounds: A clean and safe synthesis of β-hydroxynitriles
Bianchi, Gabriele,Feroci, Marta,Rossi, Leucio
experimental part, p. 3863 - 3866 (2010/01/11)
The electrogenerated cyanomethyl anion reacts with carbonyl compounds to yield the corresponding β-hydroxymtriles in moderate to high yields. The reported methodology is very clean and safe, avoiding the use of any classical base or catalyst.
Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
Matsukawa, Satoru,Kitazaki, Eri
, p. 2982 - 2984 (2008/09/20)
A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.
Metalated nitriles: Organolithium, -magnesium? and -copper exchange of α-halonitriles
Fleming, Fraser F.,Zhang, Zhiyu,Liu, Wang,Knochel, Paul
, p. 2200 - 2205 (2007/10/03)
(Chemical Equation Presented) α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by SN2 displacement whereas organocopper nitriles react by S N2′ displacement, correlating with the formation of a C-metalated nitrile.
Metalated Nitriles: Halogen - Metal Exchange with α-Halonitriles
Fleming, Fraser F.,Zhang, Zhiyu,Knochel, Paul
, p. 501 - 503 (2007/10/03)
(Equation presented) α-Halonitriles react with organometallic reagents in a facile halogen-metal exchange. The halogen-metal exchange is extremely fast with Grignard and alkyllithium reagents, generating metalated nitriles in situ with aldehyde, ketone, a
Direct conversion of α,β-unsaturated nitriles into cyanohydrins using Mn(dpm)3 catalyst, dioxygen and phenylsilane
Magnus, Philip,Scott, David A.,Fielding, Mark R.
, p. 4127 - 4129 (2007/10/03)
Treatment of α,β-unsaturated nitriles with Mn(dpm)3 (3 mol%), PhSiH3 in isopropyl alcohol in the presence of oxygen resulted in reduction and α- and β-hydroxylation.
SmI2-mediated nitrile aldol reaction
Caracoti, Andrei,Flowers II, Robert A.
, p. 3039 - 3041 (2007/10/03)
The SmI2-mediated coupling of α-bromoacetonitrile and α- bromopropionitrile with aliphatic ketones and aldehydes produces β- hydroxynitriles in good yields. Reactions typically proceed with little diastereoselectivity, but selectivity enhanceme
P(RNCH2CH2)3N-Catalyzed synthesis of β-hydroxy nitriles
Kisanga, Philip,McLeod, Dale,D'Sa, Bosco,Verkade, John
, p. 3090 - 3094 (2007/10/03)
We herein report the successful synthesis of β-hydroxy nitriles in very good to excellent yields from aldehydes and ketones in a simple reaction that is promoted by strong nonionic bases of the title type. The reaction occurs in the presence of magnesium salts which activate the carbonyl group and stabilizes the enolate thus produced.
Aryl halides as precursors of electrogenerated bases. Utilization in coupling reactions of acetonitrile with various electrophilic compounds
Barhdadi, Rachid,Gal, Jacques,Heintz, Monique,Troupel, Michel,Perichon, Jacques
, p. 5091 - 5098 (2007/10/02)
An electrochemical alternative to classical cyanomethylation is possible by using electrogenerated bases (EGBs), obtained by electroreduction of aryl halides in an undivided cell fitted with a cadmium coated cathode and a sacrificial magnesium anode. Acetonitrile is used both as solvent and as hydrogen-active compound. A coupling reaction with various electrophilic compounds was carried out. When the electrophilic compound was present from the beginning of the electrolysis, the expected coupling product with the cyanomethyl anion was obtained. If the electrophilic compound was added only after complete electrolysis of the aryl halide, dimerization of the cyanomethyl anion and a coupling reaction between the dimer anion and the electrophilic compound were observed.
